SU514565A3 - Method for producing alkanolamine derivatives - Google Patents

Description

(54) METHOD FOR OBTAINING ALKANOLAMINE DERIVATIVES

Th, a

OCH CHOHCH NHR

Gclbx

where R is alkyl or oxyalkyl containing up to 6 carbon atoms;

Cs is alkanoyl containing up to 6 carbon atoms, or “arbamoyl, alkyl carbamoyl, alkenylcarbamoyl, in which alkyl and alkenyl contain up to 6 carbon atoms, or carbazoyl;

And - alkyla with 1-5 carbon atoms;

n - 1 or 2;

Ra is the same or different with n equal to 2, hydrogen, halo, nitro, hydroxy, cyano, al: kil, alkenyl, acyl or alkoxycarbonyl containing up to 6 carbon atoms, cycloalkyl containing up to 8 carbon atoms ./0

where XCH-CHg p (or) CHOH-CH Y groups,

where Y is halo) d, and all other symbols correspond to the above,

is reacted with an amine of the general formula NH.R, where R has the indicated meanings.

However, in the literature there are no data on alkanolamine derivatives, o; they are found in the tethered method, however, the latter are more active compounds than the known ones. The compounds of the proposed method differ in their structure from the known ones described above in that the carbamoylalkyl group is linked to the aromatic core through the hydrogen atom, and also in that the two side chains in the benzene core are located in the ortho-position relative to each other to a friend. In accordance with the invention, a method is described for the preparation of derivatives of alkanols on common forms -OClbCHOllCHR NHS OA-CONSV where R is hydrogen, "or alkyl, which can be replaced by one or several substituents selected from: or aryloxy, cycloalkyl or alkenyl; R is hydrogen, or alkyl; R is hydrogen or alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, alkenyl or aralkyl, or R2 together With the adjacent nitrogen atom to which they are attached form a heterocycle, a clinical ring; R-hydrogen or halo, or alkyl, alkeiyl, hydroxy, alkylthio, alkoxy, alkenyl OXY, aralkoxy, or haloalkyl; L is alkylene, as well as salts of these compounds with acids. A preferred alkanolamine group includes compounds of the formula OCHzCHOHCHsNHR OSLEGSON in which R, R3 and R are as defined above; Of these compounds, the recommended compounds are those in which R is isopropyl, Tuoeg-butyl, or 2-hydroxy-1,1-dimethylethyl, R is hydrogen or alkyl, alkenyl or cycloalkyl, each of which contains up to 6 carbon atoms. Particularly preferred of this group are compounds in which W is hydrogen, methyl, ethyl or allyl, and R is hydrogen. The described method is that a compound of the formula XCHR is NRR, where R and R are as defined above, R is hydrogen OR a blocking group, and X is a DR group, CHO-CH- or YCH2-CH, where R is hydrogen or a blocking group, and Y - replaceable by radio.cal, is reacted with a phenol of the formula OA-CONR lf RR and R have the meanings given above, then if one or both of R and R are blocking groups, these blocking groups are removed, then, if necessary, a compound in which one or more of the radicals R, R and R-alkenyl can be reduced to the corresponding It contains a compound in which one or more of the R, R and R radicals are alkyl radicals. Target products are isolated by known methods in the form of bases, Salts, racemate or optically active antipodes. Example 1. A mixture of 3.34 g of 4-hydroxyphenoacetamide, 1.6 g of sodium hydroxide, 4 g of 1-chloro-3-g / er-butylaminopropanol-2 hydrochloride and 100 ml of ethanol is heated under reflux for 24 hours, and then filtered. The filtrate is evaporated to dryness under vacuum. The residue is partitioned between 100 ml of ethyl acetate and 50 ml of aqueous 1N. sodium hydroxide solution, and the organic layer is separated, washed five times with 20 ml portions of water, dried and evaporated to dryness. The solid residue is recrystallized from a mixture of ethyl acetate and luteral ether (t. Kip. 60-80 ° C) and receive 1- (4-carbamoylmethoxyphenoxy) -3 - t / ze 7 - butylamine 1-propanol-2 with so pl. 88-90 ° C. Example 2. The process described in example 1 was repeated, using the corresponding phenol and the corresponding 1-chloro-3-a1 Minopropanol-2 hydrochloride as starting reagents. As a result, the compounds listed in the table were obtained. OCHjCHOHCHjNHR rNlltOtHzO

2) 30 - / VoUHjCHOHtHzNHIl

R NHCOUtt

 Vof- b CHOH CHjNHR OCH.CONHE

.//

y-oengPenkknny O-A-CONRR